Vilsmeier–Haack Type Formylation on 6-Aryl-1,4-dithiafulvenes and Syntheses of Novel Extended Tetrathiafulvalene Donors

Atsushi Fujioka; Takashi Kubo; Miho Watanabe; Masafumi Ueda; Hisakazu Miyamoto; Yohji Misaki

doi:10.1055/s-0035-1560400

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(06): 845-854
DOI: 10.1055/s-0035-1560400

paper

Vilsmeier–Haack Type Formylation on 6-Aryl-1,4-dithiafulvenes and Syntheses of Novel Extended Tetrathiafulvalene Donors

Atsushi Fujioka

^aDepartment of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan eMail: misaki.yohji.mx@ehime-u.ac.jp

,

Takashi Kubo

^aDepartment of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan eMail: misaki.yohji.mx@ehime-u.ac.jp

,

Miho Watanabe

^aDepartment of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan eMail: misaki.yohji.mx@ehime-u.ac.jp

,

Masafumi Ueda

^aDepartment of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan eMail: misaki.yohji.mx@ehime-u.ac.jp

,

Hisakazu Miyamoto

^aDepartment of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan eMail: misaki.yohji.mx@ehime-u.ac.jp

,

Yohji Misaki*

^aDepartment of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan eMail: misaki.yohji.mx@ehime-u.ac.jp

^bElements Strategy Initiative for Catalysts and Batteries (ESICB), Kyoto University, Katsura, Kyoto 615-8520, Japan

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Abstract

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Abstract

The Vilsmeier–Haack type formylations on various 6-aryl-1,4-dithiafulvenes were examined. The furyl derivatives on treatment with an excess of POCl₃ in DMF at room temperature mainly afforded dialdehydes substituted at the 6-position and the furan ring, while the thienyl derivatives and the phenyl derivatives mainly gave monoformylated derivatives substituted at the 6-position. The obtained mono- and dialdehydes were converted into monoaryl-substituted 2,2′-ethanediylidene-bis(1,3-dithiole) derivatives and heteroaromatic ring-inserted [3]dendralene derivatives with triple 1,3-dithiol-2-ylidenes and their TTF-fused analogues. Electrochemical properties of the new π-electron donors were also investigated by cyclic voltammetry.

Key words

tetrathiafulvalene - redox - cyclic voltammetry - Vilsmeier–Haack reaction - heterocycles

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Referenzen

References
1 Present address: Department of General Education of Science, National Institute of Technology, Kurume College, Komorino, Kurume 830-8555, Japan.

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